CN104768623B - 用于纯化具有羧酸酯端基的(全)氟聚醚的方法 - Google Patents
用于纯化具有羧酸酯端基的(全)氟聚醚的方法 Download PDFInfo
- Publication number
- CN104768623B CN104768623B CN201380057794.9A CN201380057794A CN104768623B CN 104768623 B CN104768623 B CN 104768623B CN 201380057794 A CN201380057794 A CN 201380057794A CN 104768623 B CN104768623 B CN 104768623B
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- mixture
- pfpe
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- functional
- chain
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- 238000000034 method Methods 0.000 title claims abstract description 63
- 150000007942 carboxylates Chemical group 0.000 title claims abstract description 29
- 238000000746 purification Methods 0.000 title claims abstract 3
- 230000008569 process Effects 0.000 title abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 108
- 238000004587 chromatography analysis Methods 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- 239000007790 solid phase Substances 0.000 claims description 27
- 239000007791 liquid phase Substances 0.000 claims description 22
- 239000000741 silica gel Substances 0.000 claims description 18
- 229910002027 silica gel Inorganic materials 0.000 claims description 18
- 239000000725 suspension Substances 0.000 claims description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 17
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 125000000524 functional group Chemical group 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 229920000570 polyether Polymers 0.000 claims description 10
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 9
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 150000001298 alcohols Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 230000003252 repetitive effect Effects 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 239000003849 aromatic solvent Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 4
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical compound FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 claims 1
- 239000003791 organic solvent mixture Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 claims 1
- 235000012239 silicon dioxide Nutrition 0.000 claims 1
- 239000002904 solvent Substances 0.000 description 19
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 17
- 230000009977 dual effect Effects 0.000 description 13
- 239000007787 solid Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 239000012071 phase Substances 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- 238000004293 19F NMR spectroscopy Methods 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000003682 fluorination reaction Methods 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000002798 polar solvent Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000003463 adsorbent Substances 0.000 description 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- -1 carboxyl compound Chemical class 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- AURUIZOPZBDIGG-UHFFFAOYSA-N 3,3,4,4,5,6-hexafluoro-5,6-dimethylcyclohexene Chemical compound FC1(C(C(C(C=C1)(C)F)(C)F)(F)F)F AURUIZOPZBDIGG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminium flouride Chemical compound F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 150000001265 acyl fluorides Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 210000004899 c-terminal region Anatomy 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229920002313 fluoropolymer Polymers 0.000 description 2
- 239000004811 fluoropolymer Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000011210 chromatographic step Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000005686 electrostatic field Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002576 ketones Chemical group 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 230000005501 phase interface Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/42—Selective adsorption, e.g. chromatography characterised by the development mode, e.g. by displacement or by elution
- B01D15/424—Elution mode
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/002—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds
- C08G65/005—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens
- C08G65/007—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/30—Post-polymerisation treatment, e.g. recovery, purification, drying
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/46—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing halogen
- C08G2650/48—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing halogen containing fluorine, e.g. perfluropolyethers
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyethers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12191288.5 | 2012-11-05 | ||
| EP12191288 | 2012-11-05 | ||
| PCT/EP2013/072679 WO2014067981A1 (en) | 2012-11-05 | 2013-10-30 | Process for the purification of (per)fluoropolyethers with carboxylate end groups |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104768623A CN104768623A (zh) | 2015-07-08 |
| CN104768623B true CN104768623B (zh) | 2017-02-08 |
Family
ID=47143687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201380057794.9A Active CN104768623B (zh) | 2012-11-05 | 2013-10-30 | 用于纯化具有羧酸酯端基的(全)氟聚醚的方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9370733B2 (de) |
| EP (1) | EP2914358B1 (de) |
| JP (1) | JP6530715B2 (de) |
| CN (1) | CN104768623B (de) |
| WO (1) | WO2014067981A1 (de) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106084112B (zh) * | 2011-05-18 | 2018-03-30 | 旭硝子株式会社 | 含氟共聚物及离子交换膜 |
| CN103534283B (zh) * | 2011-05-18 | 2016-10-12 | 旭硝子株式会社 | 含氟共聚物的制造方法 |
| EP3037455B1 (de) * | 2013-08-23 | 2018-10-31 | Daikin Industries, Ltd. | Verfahren zur trennung einer carbonsäureverbindung mit perfluor(poly)ethergruppe |
| JP6513053B2 (ja) * | 2016-06-13 | 2019-05-15 | 信越化学工業株式会社 | 片末端カルボキシル基含有パーフルオロポリエーテル化合物を含む組成物の製造方法 |
| WO2019163712A1 (ja) * | 2018-02-21 | 2019-08-29 | ダイキン工業株式会社 | （ポリ）エーテル基含有モノカルボン酸化合物の製造方法 |
| JP2019214704A (ja) | 2018-06-08 | 2019-12-19 | 信越化学工業株式会社 | パーフルオロポリエーテル化合物の分離精製方法 |
| CN113866314B (zh) * | 2021-10-09 | 2022-09-09 | 上海睿易环境科技有限公司 | 一种测定土壤和沉积物中九氟丁基乙基醚含量的方法 |
| CN116874765A (zh) * | 2022-06-23 | 2023-10-13 | 浙江大学 | 液液萃取分离单羧酸盐端基全氟聚醚和双羧酸盐端基全氟聚醚的方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101466769A (zh) * | 2006-04-06 | 2009-06-24 | 索尔维索莱克西斯公司 | 制备高纯度单羧酸类全氟聚醚的方法 |
| WO2010130628A1 (en) * | 2009-05-15 | 2010-11-18 | Solvay Solexis S.P.A. | Process for the purification of polyol pfpe derivatives |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1104482A (en) | 1964-04-09 | 1968-02-28 | Montedison Spa | Perfluoro-olefin derivatives |
| US3442942A (en) | 1964-04-09 | 1969-05-06 | Montedison Spa | Fluorinated oxygen containing acyl fluorides |
| CA1263405A (en) | 1984-05-23 | 1989-11-28 | Giantommaso Viola | Process for preparing neutral and functional perfluoropolyethers with controlled molecular weight |
| IT1229845B (it) | 1989-04-20 | 1991-09-13 | Ausimont Srl | Procedimento per la preparazione di perfluoropolieteri perossidici. |
| IT1251965B (it) | 1991-10-21 | 1995-05-27 | Ausimont Spa | Procedimento per separare tra loro le specie non funzionali, monofunzionali e bifunzionali presenti nei perfluoropoliossialchileni. |
| IT1251964B (it) | 1991-10-21 | 1995-05-27 | Ausimont Spa | Procedimento per separare tra loro specie non funzionali, monofunzionali e bifunzionali presenti nei perfluoropoliossialchileni. |
| US5919614A (en) | 1994-10-19 | 1999-07-06 | Lifecell Corporation | Composition comprising three platelet lesion inhibitors for platelet storage |
| IT1282628B1 (it) | 1996-02-14 | 1998-03-31 | Ausimont Spa | Processo per la preparazione di perfluoropolieteri perossidici |
| IT1283646B1 (it) | 1996-08-02 | 1998-04-23 | Ausimont Spa | Processo di preparazione di perfluoropolieteri |
| IT1290462B1 (it) | 1997-04-08 | 1998-12-03 | Ausimont Spa | Polimeri idrogenati modificati |
| ITMI20041370A1 (it) | 2004-07-09 | 2004-10-09 | Solvay Solexis Spa | Separazione di perfluioropolirteri -pepe-bifunzionali a termninazione-ch20h dalle loro miscele con pepe monofunzionali-ch2oh |
| JP5235026B2 (ja) | 2010-09-28 | 2013-07-10 | 信越化学工業株式会社 | フルオロオキシアルキレン基含有ポリマー組成物および該組成物を含む表面処理剤並びに該表面処理剤で表面処理された物品 |
-
2013
- 2013-10-30 CN CN201380057794.9A patent/CN104768623B/zh active Active
- 2013-10-30 EP EP13783931.2A patent/EP2914358B1/de active Active
- 2013-10-30 US US14/440,821 patent/US9370733B2/en active Active
- 2013-10-30 JP JP2015540108A patent/JP6530715B2/ja active Active
- 2013-10-30 WO PCT/EP2013/072679 patent/WO2014067981A1/en active Application Filing
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101466769A (zh) * | 2006-04-06 | 2009-06-24 | 索尔维索莱克西斯公司 | 制备高纯度单羧酸类全氟聚醚的方法 |
| WO2010130628A1 (en) * | 2009-05-15 | 2010-11-18 | Solvay Solexis S.P.A. | Process for the purification of polyol pfpe derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| JP6530715B2 (ja) | 2019-06-12 |
| US20150251107A1 (en) | 2015-09-10 |
| WO2014067981A1 (en) | 2014-05-08 |
| EP2914358B1 (de) | 2017-03-08 |
| JP2015535017A (ja) | 2015-12-07 |
| US9370733B2 (en) | 2016-06-21 |
| EP2914358A1 (de) | 2015-09-09 |
| CN104768623A (zh) | 2015-07-08 |
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